ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Nucleosides and Nucleotides, Part 11. Phosphorylation of 1-(2′-Desoxy-β-D-ribofuranosyl)-2(1H)-pyridon and its Behaviour in the Synthesis of DinucleotidesThe behaviour of the unnatural nucleoside 1-(2′-deoxy-β-D-ribofuranosyl)-2(1H)-pyridon (Πd, 1) in the synthesis of dinucleotides with purine deoxynucleotides was studied. The optimized preparation of the protected dinucleoside phosphates (MeOTr) Πd pGibd (5) and (MeOTr) Πd pAbzd (7) using the diester method of Khorana with DCC as condensing agent is described. The removal of the N-acyl- and p-methoxytrityl groups was effected by successive treatment with conc. ammonia solution and acetic acid/water 1:1 at 23° yielding the free dinucleoside phosphates ΠdpGd (9) and ΠdpAd (11). In a similar way, starting from (CNEt) pΠd(15), the dinucleotides pΠdpGibd (16), pΠdpGd (18), pΠdpAbzd (17) and pΠdpAd (19) were synthesized.The nucleotide 1-(5′-O-Phosphoryl-2′-deoxy-β-D-ribofuranosyl)-2(1H)-pyridon (pΠd, 3) was prepared in excellent yield by selective phosphorylation of Πd (1) using phosphorylchloride in triethyl phosphate at -40°. Deoxyadenosine was phosphorylated in the same way.The compounds were characterized by UV. spectroscopy, chromatography and enzymatic degradation.
Zusätzliches Material:
2 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19780610513
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